Synthesis of a heparan sulfate tetrasaccharide using automated glycan assembly.

Pongener, Imlirenla; Sletten, Eric T.; Danglad-Flores, José Angél; Seeberger, Peter H.; Miller, Gavin J

doi:10.1039/d3ob01909h

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Synthesis of a heparan sulfate tetrasaccharide using automated glycan assembly.

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Sletten, Eric T.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Danglad-Flores, José Angél
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger, Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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引用

Pongener, I., Sletten, E. T., Danglad-Flores, J. A., Seeberger, P. H., & Miller, G. J. (2024). Synthesis of a heparan sulfate tetrasaccharide using automated glycan assembly. Organic & Biomolecular Chemistry, 22(7), 1395-1399. doi:10.1039/d3ob01909h.

引用: https://hdl.handle.net/21.11116/0000-000E-66D0-4

要旨

Herein we utilise automated glycan assembly to complete solid-phase synthesis of defined heparan sulfate oligosaccharides, employing challenging D-glucuronate disaccharide donors. Using an orthogonally protected D-GlcN-alpha-D-GlcA donor, milligram-scale synthesis of a heparan sulfate tetrasaccharide is completed in 18% yield over five steps. Furthermore, orthogonal protecting groups enabled regiospecific on-resin 6-O-sulfation. This methodology provides an important benchmark for the rapid assembly of biologically relevant heparan sulfate sequences.